Sent to Chicago
by RegallyCharmingOutlawQueen
Summary: In 1923, young impressionable Regina Mills was sent Chicago to live with her father. Her first night in town, she stumbles upon a secret Speakeasy... The Mill. Where she falls in love, learns secrets she never expected, and awaits danger. If you want a second chapter, you gotta review and let me know your thoughts. Otherwise I'm just gonna assume it's not worth continuing.
1. Chapter 1

**AN: New idea for a story. Set in the 1920's. AU. Read and Review! :D**

1923:

At 17 years old, she was expected to be an upstanding debutante. Her mother Cora, coached her to be an excellent lady, taking her to balls, hosting tea parties in the White's Mansion in New York City. She had been all of those things in public, secretly she wanted to be a flapper. Regina Mills was not a debutante. And that's how she ended up on a train to Chicago. To live with her father, of course Regina hated her father. He owned a little cleaning shoppe in downtown Chicago. Of course this was her punishment. Give the family a bad name and they cast you away. Her mother and father had split right after Regina was born, leaving her and her mother to move to New York with her 'new father' Leo, a few years later, her sister was born.. Gloria. Of course Gloria was the perfect little lady. Already promised to a handsome suitor. But Regina, she was trouble to Her mother and stepfather.

it started when she bobbed her hair, her hair had been down the middle of her back, one day after school she just, snipped it all off. Leaving it in a bob. Like all of the flappers wore. In the back of her closet, she had a gold sequined dress, it hung from her perfectly. A feathered headband and A pair of shoes to match. The thing that set her mother off, was finding her daughter, climbing through a window at three am, dressed as a flapper, with gin on her breath. The next morning Regina was put on a plane with all of her things and some money.

Her father had sent his assistant, Robert, to escort her to his home. He was probably busy with his business. He ran a cleaning service. The only thing Regina hated about her father was that he was a prohibitionist, and a politician. In fact he practically ran the campaign against alcohol sales. It drove her mad. On top of that, old Henry was a religious person. Always preaching about how the good Lord did this... And that.

Her head was leaned against the window, her hair that was once coiffed, was now a bit messy from falling asleep against said window. She watched from her window as the train pulled into the station. A few minutes later she was stepping off with her bags. She didn't know here Robert would be, nor where to go to find her ride. She stopped as soon as she stepped off the train and asked the man whom had helped her off.

"if I were being picked up... Where would I go?" She asked sweetly.

"On the other side of the station doll." He said nicely and hopped back onto the train.

To be honest, she was a bit afraid as she walked through the station To get to the other side. Once she walked through the doors to the other side of the train station she saw several different cars, but was immediately drawn to a man leaning against his car, smoking a cigarette. He looked like an Italian mobster to be honest. From his shoes, to his black tailored suit, all the way up to his fedora. she took him in for a moment before seeing the sign in his hand. It simply said: Regina. She walked up towards him and have her best soft smile. "Robert... I presume?"

"Indeed." He said, flicking his cigarette and getting off of the car, which she recognized as a LaFayette. "So, you're Ol' Henry's infamous daughter eh?"

"Matter of fact I am. Where is he?" She said, trying not to make note on how attractive Robert was. She noticed him watching her as well and smiled brightly. "Well quit acting like a dewdropper and take me into town." She grinned and he took her bag.

Once in the car, she watched him intently. "You look like a mobster you know.." She said with a chuckled and he turned to look at her for a brief moment.

"You look a bit like a flapper. Got sent to your father for sneaking out to a party.. " he said with a teasing tone.

"If you knew Cora, you'd understand why." She winked and turned back to look out of the car. The rest of the way there was pretty silent, they turned into a neighborhood full of really nice houses and she frowned. Last time she had seen her father he lived in a small house downtown.

"I see he came upon some money." She said as they pulled up to a rather large house, a Flivver sitting in front of it.

"You could say that." He chuckled and hopped out of the car, grabbing her bag and opening the door for her. "A lady like you should show off her gams, I bet you have nice ones." He whispered as she got out. His words made her blush.

Before she could give a witty retort of her own, her father stepped out of the front door with a smile. "Regina." He greeted. "Look how you have grown! What did you do to your hair? You look like one of those awful gin-joint flappers." Robert bit back a chuckle and Regina could tell he wanted to laugh. "I trust Robert took good care of you?"

"Yes father he did." she said with a sincere smile.

"i was just on my way out, but I will show you to your room to unpack before I go." he said, wrapping his arm around her back. "Thank you Robert." he smiled.

"Not a problem sir. If she needs anything else let me know." He said it with a twinkle in his eyes and looked towards Regina for a moment. "Nice to meet you." he tipped his hat to her and was off.

Her father'a house was gorgeous. When she said he must've come into money, obviously Robert was not kidding... He must have come into a boat load. He led her up the stair and down a hallway before opening a door to a rather large room. There was a bed big enough for three people, a vanity and a large closet. "Here you are dear. Now I must be going."

She smiled, said her goodbyes and kissed his cheek before he left. Once he was gone she decided to go see a flick. She'd seen a theater a couple blocks away. Her father technically didn't say she had to stay at the house anyways. She quickly changed, put on a new face and headed in the direction to the theater. _The Covered Wagon._ It seemed good.

She sat in the theater while the movie was playing, focused intently on what was going on. It was definitely worth possibly getting in more trouble to go see. She stepped out of the theater with a smile and nearly tripped, but before she hit the ground she felt strong arms wrap around her. once she got her balance, she turned. A handsome gentleman had caught her. He was sheik she though.

"Almost lost yourself to the ground." He flashed his best smile and grinned. "Be careful."

"Regina." She stuck out her hand and the gentleman kissed it. "Thank you."

"Anything for a doll face like you. I'm Daniel. Say.. I got to run, but.." he pulled a card from his pocket, "I'll be at this address later if you'd like to continue our conversation."

Regina took the card and look it over, when she looked up, he was gone. She frowned and headed back to her father's home.

Her father hadn't come home yet, the maid had come and went by the time Regina had finished getting ready to meet Daniel. he had been cute, but her mind continued to travel to Robert.. He had a mystery about him that she wanted to know more about. He was way more interesting than the dull boys at the academy in New York. She was in the center of flapper city, surely it was more interesting than New York.

She had cleaned up, slipped on her only dress, the gold one. Her feathered hair band and a fresh face of make up... Which included her blood red lips. A once-over in her mirror made her smile. She knew she had 'it'.

Regina handed the address Daniel had given her to the cab driver and he drove silently to wherever it was. It wasn't until the cabbie stopped in front of her fathers cleaners that she questioned him.

"Listen Doll, you have me the address, I took you to it."

She sighed, handed him some cash and got out. She stood by the entrance of an alley, right next to the store and looked around. There was a man standing by a door and she sucked in a breath, _be brave, _she told herself and walked up to the man.

"I was supposed to meet someone named Daniel here, but I do not see anywhere to meet him.." She said.

"Ahh you must be new. Just follow me doll face." He was English, she could tell by his accent. "Your name?"

"Regina."

"Very beautiful. Im Killian." He knocked on a door in the alleyway three times and a little peepdoor slid open. "Clodhoppers." He said to the most furiously bright green eyes she had ever seen, and then a door opened.

"A juice joint." She grinned. "Wonderful." She stepped passed the rather large man with green eyes and down some stairs before walking into a smoke filled room.

Everything was red and gold. To her right were a set of tables that were dimly lit, a few people were sitting at them. To the front of her was the bar about twenty feet ahead, behind the bar were many, many bottlea of what she assumed were giggle juice. There were bottles of different colors shapes and sizes, at leaat hundreds on a set of three shelves. To her left was a stage, with a small dance floor and a doorway which most likely lead to the back.

she sat at the bar and awaited the bartender, "Give me the best you got." She flashed him a sexy smile before he turned to make her drink. She turned on the barstool and froze exactly the way she was. Her legs were crossed, the slit in her dress showing off more leg than legal.

"Robert?" She said nervously. What was he doing here? What was a juice joint doing under her daddy's shop?

"I told you, you have nice gams."

**AN: So... I'll only continue if you guys want me to... It's really AU... But I promise It'll be good! If you want a chapter two, review.**


	2. Chapter 2

**AN: So most of you figured out that Robert was Robin.. I would have called him Robin, but that name doesn't really fit with the story, neither does Snow so I named her Gloria. Lol. So far we've met Regina, her father, Robin (Robert), Snow, Hook and Daniel. Now there are two more men from OUAT that will appear in this story.. And eventually you'll realize why. Lol. But, here is the second installment, so if you want me to continue you must review and give me your thoughts. Alrighty?**

Regina giggled at Robert, she could feel his heated gaze all over her. She heard the smooth sound of jazz beginning to waft through the speakeasy. She turned to the stage and smiled. The man who had let her in... Killian, she believe to be his name, was standing onstage next to a blonde woman. She watched as they introduced themselves.

Killian spoke first. "Now, I'd like everyone to give a big welcome to our new regular, Emma Swan." There was a series of low claps and then the band began to play. She turned back to Robert, and jumped a little in surprise to find him in a slightly heated argument with none other than Daniel. She could barely make out their words. What she did make out was 'Do you know who she is?' And 'She is Ol' Henry's little girl'.

She tilted her head and bit her lip. She focused hard on their lips and stood quickly. "Daniel, I do believe you invited me.. So, where is my dance?" She was slowly putting the pieces together.

"Why of course." he shot Robert a look, basocially tell him to chill out, and he put his hand out for Regina to take.

Regina took his hand and followed hi out to the dance floor. She could feel Robert's eyes on her. They danced for a fee songs until Robert stepped next to them.

"Can I cut in?" He looked at Daniel.

"Sure " he smiled and stepped back as a slow jazz began to play.

Robert pulled Regina closer as they swayed to the song. And she looked at him. "So tell me.. What is the name if this joint?" She knew somehow her father had to be connected to this speakeasy. why else would it be under his store? Why would they have been whispering about her and her father? Why else would Robert be here? She needed to get more infoemotion out of him.

"The Mill.." She frowned.. As she opened her mouth to ask another question, the music stopped and he pulled her back to the bar. Robert raised his fingers to the bartender, signaling for two drinks.

"Make her's a little light." she heard him mumble And she frowned, scoouting onto her stool with grace. The bartender leaned against the bar in front of her and began to talk to Robert.

"Man, no matter how many times I count the books, the count keeps coming out off. I think I'm missing a number." He pulled a stack of ruffled papers out from under the bar.

"Let me see those?" She said, pulling the stack tiwards her.

"Knock yourself out doll face. I can't seem to get it right."

Robert laughed. "Maybe it's because you're always so busy.. Ain't got time for anything else! Ol' man would have your behind if those books came out wrong."

Regina wasn't paying attention to the men's chitchat, she was focusing on the books. Within a few moments she was handing then back over to the bartender, pointing out a few things. "Here's where you messed up, see that there? You mistook it for a different number. This number is your sales, and this is your stock as of right now." She grinned and picked up her glass.

"Well I believe you earned my name. I'm Graham." He looked her over and winked then turned back to Robert.. "She sure is a dish.. Mm." He smirked and then frowned. "Uh oh.. Jeff's here." He shook his head and turned to get the man his usual.

"Who's Jeff?" Regina asked with a frown.

"He's a regular.. He kinda has a part in this place. No one really likes him. Or trusts him for that matter. You gotta really know your onions before messing with that guy."

The entire time, Regina was piecing things together.. So far, she had come to the conclusion that maybe, things weren't what they seemed in Chicago. She watched Robert get up to take a phone call and not even moments later the man they had called Jeff, slid into the seat beside her.

"How about I get you another?" She heard from beside her after several moments of sitting at the bar listening to the jazz flow through her.

"Eh. I'm alright , I believe Ive had enough for tonight." She was smarting off to him and he could tell.

"Well then.. Looks like we've got a bearcat in the house." He retorted and turned back to Graham.

Before Regina could say anymore, Robert returned with a solemn look on his face. "Listen doll... We gotta go." He said, reaching for Regina.

"Why?" She frowned. "I was hoping to get a lookin' around the town." She stood and giggled, leaning on Robert a bit, she was rigHt, she had had enough for the night.

"Ol' Henry's been shot."

Robert had given her a ride, the entire ride was spent with her sobering up quickly And Robert letting her in on the information. "He's fine. He is awake and resting now. They're gonna let us all see him."

Even though she hated her father she had been afraid, honestly.. She breathed once she saw her father sitting on a bed. "Daddy." She said softly.

Henry looked at Robert, "Why did you bring her here?" He said as Regina hugged him.

"Uh.. Well, see. She went to see a flick earlier and ran into Daniel.." She watched as her father turned to Daniel, and frowned.

"I know where this is going, I can tell by the way she is dressed." He frowned and stepped back to take in his daughter's appearance. "You were at The Mill."

"Yes." She said, "And I don't regret it. It was fun." The door to his room opened and Killian, Graham, And Jeff walked in. "Daddy.." She said as she turned to see all of the people she'd met at The Mill. "I think you owe me an explanation."

**AN: So, what do you think her father will say? Read and revie. For a third chapter. **


	3. Chapter 3

**AN: Here's chapter three. So, if you guys have any suggestions or anything.. Feel free to let me know. I thrive on reviews! So please read, and then hit the little review button and type away! :D**

She watched as her father paused, and looked over at Robert.. "Well dear, I own The Mill.. And every man in this room.. Is helping me keep it under wraps... So to speak.. Wouldn't want to get pinched." He said with a chuckle.

She bit her lip and frowned. "So you're apart of the prohibition campaign... But you run a juice joint?" She found it very conflicting.

"Well, it's not all that its cracked up to be dear. It seems The Mill may be out of commission for a few Months seeing that I am bed ridden until then and there is no one who can take my place."

Robert piped up then, he took of his fedora and smoothed a hand over his messy brown tousled hair. "Aye now. You taught me all of that stuff months ago. I can run it."

Henry shook his head. Regina had been standing there watching them talk about it, she was interested in a challenge, a thrill.. Maybe even an adventure. She bit her lip and tilted her head. "I can do it." she mumbled as her father told Robert that his temper would get him and the joint pinched, especially if he acted like a hooligan and beat up the hooch guy again.

Both men turned to look at her. "What?" Her father and Robert both said.

"I can do it." She said. "I already fixed your books, I took secretarial classes and business.. I can run it."

Her father stared at her for a moment and Robert piped in. "I seen her do it. She did pretty good."

"There is more to it than just running it. You have to make sure that the feds don't catch wind of it, You have to be in charge of the shipments and everything." Henry took a deep breath and sighed. He didn't want his daughter in danger, but she was his only hope. He knew if she didn't run it, Then he would have to shut it down.

She nodded. "I can learn." She was up for the adventure.

"Pick one of the boys then." He said, almost regretting his decision. "Robert, Daniel, Graham, Jeff or Killian.. All of the men know the club, all of them have specific.. Jobs to help me out." he said as he signalled for Robert to leave the room for a moment.

"I don't understand.." Regina frowned and sat down as her father moved to lay back into his bed. "They all have jobs?"

"I'll explain.. Robert is my right hand man. He knows everything to do with The Mill.. He just has a temper and can't run it himself.. He can do everything from charming the customers, to shaking down people who owe me money. He knows the business too. Whereas Jeff, he is a copper. He keeps the force from getting wind of the mill. He's my protection in the law enforcement. He keeps everything under wraps for me. Daniel.. He recruits people to come to the club.. Like he accidentally did for you today. He uses his charm to get young ladies, and others to come visit. Graham is my bartender. He knows a lot, but he fumbles easily. And Killian is my entertainment. He wouldn't be of much help if you ask me."

She listened carefully to her father, her mind already made up. Robert was to be her right hand man, as he had been for her father. The bad thing was.. If her father found out her attraction to him, she would be in trouble, as would Robert.

"Robert can help me. I choose him daddy." She said with confidence.

"I admire your straight-forwardness." He said, and then called Robert back in. "Its settled.. Tomorrow, you are to begin showing her what to do, how to do it.. And I prefer you begin before the joint opens. So, I'd go rest up baby doll." Henry said and smiled, "Now let me get some rest."

She kissed her father's head and told him goodbye before leaving his room with Robert. They walked silently to his car and the whole ride to her father's house was silent. She frowned a little once they got there and turned to Robert. "Pick me up a little earlier tomorrow.."

"You mean today?" Robert smirked a little, the morning Sun was beginning to peak through the clouds, causing the sky to be a beautiful mixture of light pinks and purples. "Its morning."

She shook her head and laughed a little. "Yeah okay then. Today."

"May I ask why?" he said, a hint of flirtation in his voice. "I'm not sure Ol' Henry would appreciate you spending non-work related time with me."

"Oh, I'm sure he'd get over it.. Besides. This girl needs a new wardrobe if she is going to run an illegal gin joint." She smirked and ran her fingers through her bobbed hair. "Maybe get my hair done too."

"Looks like I am going to have a long say with you Miss Mills." Robert said with a tiny little grin. "And I'm not so sure that I even mind it." Oh Henry would kill him for flirting with his little girl. "I will see you in a few hours then."

She watched him as he got out and opened the door to his car for her so that she could get out. She smiled and thanked him. "Until then. Mister Locksley." She had a smirk on her face that would bring a grown man to his knees.

"The same to you Miss Mills." He would be sent to Hades for him impure thoughts.

Regina ran up her front steps and opened the door. She watched him leave in his car, practically melting. 'Oh goodness.' she thought as she ran upstairs, cleaned herself up and laid in bed.

It took her a bit, but finally she fell into a peaceful state of rest.

She woke up to the sound a car horn and frowned. She walked sleeping over to her window and opened it and she immediately woke up to the sight out the window. "I must've over slept!" She called out the window and down to Robert. "I'll be just a minute!"

He laughed and shook his head. "I'll be waiting!" he called back up to her and lit a cigarette as he leant against his car.

It took her approximately twenty minutes to scramble around and find something decent to wear, five minutes to apply the smolesting of what could be considered make up. She looked like death warmed over, at least... She thought she did.

On the other hand, as she stepped out of the house and walked down the steps to Roberts car, he cat called her.. Several times in fact. She was blushing by the time she made it to the car. He held open the door and she sat down in the passenger's seat.

After he got into the car, he turned to her. "Where to doll face?" He turned on the car and Regina bit her lip.

"When in Chicago.. Right? Take me anywhere.." She flirted a little and her eyes gazed over him.. In all honesty, Regina had never gone all the way witg a boy. Sure, she made out with Andrew McClure at a party she went to in New York and he tried to feel her up.. But New York didn't have the passion Chicago had, and surely Andrew McClure didn't have that... appeal that Robert had.

Regina and Robert spent the day bouncing from Shoppe to Shoppe. Regina spent way too much money, and Robert carried her bags. Although he didn't have to and she was perfectly capable of carrying them herself, he was being a gentleman, and she adored it. She spent a little hit in every store she went to. Whether it was on shoes, dresses, hair accessories or make up.. She bought it. And when they'd finished.. She had been left with no time to go to her father's house and get dressed and ready for lesson one in running The Mill.

So, she took her bags with her and decided to get ready in the back room behind the bar, where all of the liquor was stored. Robert helped her carry her bags down there and he left the room, shutting the door behind him. She fixed her hair a bit and her make-up first before she picked out an outfit..

She h we are the door open as she was going through her clothing and a pair of strong arms wrapped around her. "I think you should wear the red one.." She heard him say.. She felt his hot breath on her neck and it sent shivers down her spine. She couldn't help but turn in his arms..

"Thank you for the suggestion Robert.." She whispered, her eyes flickered between his and his lips.. "Help me with my zipper.." She mumbled breathlessly.. She felt his hands move, and her h e art stopped. He slid the zipper down incredibly slowly, and she leaned in to kiss him, but only,a millisecond before their lips were to touch.. There was a knock on the door.

"Regina!"

It was Graham.. The bartender.

"I'm gonna go ahead and let these people in, its time to open!"

She had immediately jumped back from Robert and her hands clung to the front of her dress to keep it up. "You should go.." She was out of breath from holding it for the moments that they were so close. Robert nodded and rested a hand on her cheek.

"To be continued.." He said softly and ran his thumb below her eye before he turned and left the room.


	4. Chapter 4

Once Robert had left the room, she sighed and shook her head. She needed to be more careful. If her father were to see that, or even catch wind of that, or anything else that could possibly happen between her and Robert.. Both of them were pretty much dead. Well, at least he would be. After everything that had happened the previous day, Regina wasn't sure t b at she knew her father anymore.. What she did know was that he was a false politician, he owned a cleaning store, a juice joint behind/underneath of the cleaning store and he was successful. But, what about bis feelings and such? Shouldn't a daughter know about these things when it comes to her father?

She was broken from her reverie when Robert came down the steps once more to check on her, seeing that she was still in the same position as when he had left her the first time, he placed his hand on her cheek and let his thumb actress the soft skin over her cheekbones. "Doll face? Ey. We gotta introduce you to some of The Mills' regular customers."

"Just as long as you're by my side." She dropped the dress she had been wearing to the floor, standing before him in only her undergarments. It was her way of being flirtatious, maybe stir up a bit o' passion in this guy.. Regina picked up the red dress, it was the moat sheer out of all of the dresses she had bought thay day, and it would definitely show off her gams.

Robert, who's eyes had widened as soon as the dress began slipping down her body to the floor, watched. He watched her so intently that she could feel his eyes burning into her. He watched her pick up the red dress and he stepped closer to her grabbing her up by the waist and pinning her to the wall as his lips crushed against her's.

And that was it, she could focus anymore, her skin was on fire, she dropped the dress, but it didn't hit the floor. The fact that it didn't hit the floor concerned her, but she was too. Usy to care too much. Instead she ran her short nails into Robert's hair and pulled gently as she pulled his lower lip into her mouth. She heard him groan, she knew she did. And the second it had slipped out of his mouth and into her's, her hips bucked. They pushed forward into his and Robert knew he was done for.

Footsteps were hear coming near the backroom door and Robert quickly jumped away from Regina. She pressed her fingers to her lips, and her eyes fluttered a second. She was turned on beyond belief, and as she looked down at Robin.. She knew he was too. Regina took a deep breath and smiled at him when she noticed that her red dress was in his hand, not on the floor.

"You caught my dress when it fell?" She said softly. The footsteps that had been coming near the door had just as soon started stepping away and she breathed slow again.

"Well, seeing as I really want to see you in this dress, I wasn't letting anything happen to it." He gave her a cheeky grin and handed it to her. He gazed upon her beauty as she slipped the dress on. Her skin was like a darker ivory, not quite light... But not dark either. It amazed him actually, how long her legs actually were, even though she wasn't all that tall it seemed as if they went on for miles.

Regina had been completely ready for two minutes and she was standing there with her hands on her hips waiting for Robert to break out of his daydream. "Hey big boy.. We gotta get goin' otherwise people will miss us don't cha think?" she spoke witg a flirty tone and he blushed a little at the fact he was caught.

Robert held out his arm for her to take and grinned. "C'mon then doll, let's get to this shindig."

And with that, Regina took his arm with her's and then stepped out of the back store room area,

Regina smiling and playing the part of the sultry hostess, made her way over to the bar with Robert. "Let me have a drink before I do this, I've got to get some courage."

Robert nodded and began scanning the room for the big wigs as Graham stirred up Regina's drink. Regina crossed her legs on the barstool and her dress slid up her thigh further. Robert saw it out of the corner of his eye and groaned slightly. "You're gonna kill me..." He mumbled.

Regina just laughed and took a sip of her drink. "Find anyone worth while yet?"

"Not quite.." He said. "Just a few investors. As a matter of fact, here comes one now.." He said as a tall brunette came towards him.

"Robert." She said, her accent was foreign, one that Regina had never heard before. She tilted her head, the tall woman was utterly gorgeous. She had pale blue eyes, long toned legs, and an amazing figure, she bit back the smallest bit of jealousy and smiled. "Lucy." He said, and leaned in to give the woman a light hug. "Have you met Henry's daughter? Regina."

"No. I haven't." Lucy smiled lightly, with sympathy in her eyes. "I am so sorry about what happened to your father. He is a great man." She held Regina's hand and squeezed it lightly. "He is a... Close friend." She smiled.

Robert snorted sarcastically. "Actually she's your dad's girlfriend, but it's a hush hush thing.. His work is too dangerous, and Miss Lucille here is too pretty."

Lucy blushed. "Well thank you Robert, for traumatizing this young woman." She's sipped her drink. "It was lovely to meet you Regina, hopefully we can see each other again." She grinned and kissed the young woman's cheek before she walked off to speak with someone else.

"So, I've got a step mother who looks incredible, and is a flapper? Well then.." She laughed and Robert's hand slowly slipped up her thigh, caressing the skin..

But before he could open his mouth to speak, a loud scream resonated through the speakeasy.

**AN: Lucille is depicted in my,mind as Lucy Lawless. In case anyone was wondering. PLEASE REVIEW! Lol.**


End file.
